Organic compounds derived from urea or thiourea

ABSTRACT

Compounds of the formula ##STR1## wherein A is a hydrogen atoms, a halogen atom, a methyl group, or a methoxy group; 
     B is a hydrogen atom, a halogen atom, a methyl group, or a methoxy group, with the proviso that A and B ar not both a hydrogen atom; 
     X and Y each are an oxygen atom or a sulfur atom; 
     R is a hydrogen atom, an alkyl group, a hydroxy group, an alkoxy group, an alkoxymethyl group, an acyl group, or an alkoxycarbonyl group; 
     R 1  is a hydrogen atom, an alkyl group, a halogen substituted alkyl group, an alkoxy substituted alkyl group, an alkylthio substituted alkyl group, a cyano substituted alkyl group, a 1-cycloalkenyl group, a benzyl group, a halogen substituted benzyl group, a hydroxy group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an alkoxythiocarbonyl group, an alkylsulfonyl group, or a phenylsulfonyl group, while furthermore R and R 1  together with the group ##STR2## indicated in the above formula may form a ring system; and R 2  is a substituted or non-substituted phenyl group or a pyridyl group that may be substituted with halogen, with nitro, with cyano, or with halogenated alkyl. The compounds have strong insecticidal activity against a wide variety of insects and function according to a unique mechanism. Specifically, the compounds are active against insects in the larval stage and are absorbed by the larva via its stomach to interfere with the mechanism of metamorphoses that occurs in insects.

This application is a division Ser. No. 892,365, filed Jun. 3, 1992 nowU.S. Pat. No. 5,245,071; said application Ser. No. 892,365 being adivision of Ser. No. 882,723, filed Jul. 7, 1986 and now U.S. Pat. No.5,142,064; said application Ser. No. 882,723 being a division of Ser.No. 665,508, filed Oct. 30, 1984 and now U.S. Pat. No. 4,607,044; saidapplication Ser. No. 665,508 being a continuation of Ser. No. 302, 591,filed Sep. 15, 1981 and now abandoned; said application Ser. No. 302,591being a continuation of application Ser. No. 35,978, filed May 4, 1979and now abandoned; said application Ser. No. 35,978 being a division ofapplication Ser. No. 717,633, filed Aug. 25, 1976, now U.S. Pat. No.4,166,124; said application Ser. No. 717,633 being a division ofapplication Ser. No. 522,058, filed Nov. 8, 1974, now U.S. Pat. No.3,989,842; said application Ser. No. 522,058 being a division ofapplication Ser. No. 354,393, filed Apr. 25, 1973, now U.S. Pat. No.3,933,908; said application Ser. No. 354,393 being a division ofapplication Ser. No. 143,668, filed May 14, 1971 and now U.S. Pat. No.3,748,356.

U.S. Pat. No. 3,450,747 describes that the compoundN-(3,4-dichlorobenzoyl)-N'-(3,4-dichlorophenyl) urea has a herbicidaland/or insecticidal activity.

It has now been found that a group of new compounds indicatedhereinafter have a strong insecticidal activity.

The above-mentioned known substance proves not to have such activity.

We are concerned here with new compounds of the formula ##STR3## where Ais a hydrogen atom, a halogen atom, a methyl group of a methoxy group,

B also represents a hydrogen atom, a halogen atom, a methyl group or amethoxy group, with the proviso that A and B do not both represent ahydrogen atom,

X and Y each represent an oxygen atom or a sulfur atom,

R is a hydrogen atom, an alkyl group, a hydroxy group, an alkoxy group,an alkoxymethyl group, and acyl group or an alkoxycarbonyl group,

R₁ is a hydrogen atom, an alkyl group which may be substituted withhalogen, with alkoxy, with alkylthio or with cyano, a 1-cycloalkenylgroup, a benzyl group which may be substituted with halogen, a hydroxygroup, an alkoxy group, an acyl group, an alkoxycarbonyl group, analkoxythiocarbonyl group, an alkylsulfonyl group or a phenylsulfonylgroup, whilst furthermore R and R₁ together with the group ##STR4##indicated in the above formula may form a ring system, and R₂ representsa substituted or non-substituted phenyl group or a pyridyl group whichmay be substituted with halogen, with nitrocyano or with halogenatedalkyl. The aforementioned ring system may be represented by any of thefollowing formulae ##STR5##

In these formulae Y and R₂ have the aforementioned meanings, alk is analkyl group and alkylene is a bivalent saturated alkylene group.

If R₂ is a substituted phenyl group, the phenyl group contains at leastone substituted chosen from the group consisting of:

a) 1-3 halogen atoms,

b) 1-2 alkyl groups, possibly substituted with halogen, hydroxy, alkoxy,alkylthio, dialkyl amino, alkylsulphonyl and phenyl,

c) tri- or tetramethylene,

d) a cycloalkyl group, possibly substituted with halogen or cyano,

e) 1-2 nitro groups or cyano groups or alkoxy groups,

f) a dioxymethylene or dioxyethylene group,

g) an acyl group, which may be substituted with halogen,

h) an alkyl sulfonyl, phenyl sulfonyl, alkylthio, phenylthio or phenoxygroup, which groups may be substituted with halogen,

i) a sulfonamide group, which may alkylated, and

k) a phenyl group, which may be substituted with halogen, nitro, cyanoand halogenated alkyl.

The insecticidal activity of the above group of substances has beenfound in a biological evaluation investigation in which test solutionsand test suspensions of the active substances have been examined forbiocidal activity with respect to inter alia Aedes aegypti, Leptinotarsadecemlineata, Pieris brassica, Musca domestica and Schistocercagregaria. Each active compound has been tested in various concentration,starting form a maximum concentration of 100 mg of active substance perliter of test liquid and then, according the activity found, reducingthe concentration successively to 30, 10, 3, 1, 0.3 and 1.0 mg of activesubstance per liter of test liquid.

The results of the evaluation investigation show that the aforementionedcompounds according to the invention are active against insects in thelarval stage, and that the active substance is to be absorbed by thelarva via its stomach.

The compounds according to the invention are active against, amongstother pests, caterpillars and larvae of flies, beetles, mosquitoes,locusts, cockroaches and bugs.

More particularly it has been found that the substances according to theinvention have a completely new and hitherto unknown mechanism ofactivity, for it has been found that the substances according to theinvention interfere with the mechanism of metamorphoses which occur ininsects. Hence the substances according to the invention arespecifically active against insects. Owing to this specificity andbecause of the absence of phytotoxicity effects the compounds accordingto the invention are of importance.

From the biological evaluation investigation on which the invention isbased it has been found that especially the compounds of the followingformula have a strong insecticidal activity: ##STR6## where P and Q maybe equal or different and each represent a chlorine atom, a fluorineatom or a methyl group,

R₃ represents a hydrogen atom, an alkyl group, a benzyl group, an acylgroup or an alkoxycarbonyl group,

R₄ represents from 0-3 substituents selected from the group comprisingfrom 1 to 3 halogen atoms, an alkyl group which contains from 1 to 15carbon atoms and may be substituted with one or more halogen atoms orwith a phenyl group, a cycloalkyl group which may be substituted with atleast one halogen atom a nitro group, a cyano group, a phenyl group, athiophenyl group, a benzoyl group, a thioalkyl group and analkylsulfonyl group.

This applies in particular to the substances of the above formula inwhich R₃ represents a hydrogen atom or a lower alkyl group.

A highly potent insecticidal activity has been found in compoundsaccording to the invention which satisfy the formulae ##STR7## where Rand Q may be equal or different and each represent a chlorine atom, afluorine atom or a methyl group,

R₆ is a hydrogen atom or a lower alkyl group and R₅ represents 1-3substituents selected from the group comprising 1-3 halogen atoms, analkyl group which contains from 1 to 15 carbon atoms and may besubstituted with at least one halogen atom, and a cycloalkyl group whichmay be substituted with at least one halogen atom. More particularly ithas been ascertained that the highest activity is found in the compoundsof the above formulae in which R₅ represents one or two substituents inthe position 3 or the position 4 or the positions 3 and 4 of the phenylgroup.

It has further been found that a strong insecticidal activity is alsopresent in the substances according to the invention which may berepresented by the formula ##STR8## where R₆ is a hydrogen atom or alower alkyl group and

R₇ represents a phenyl group which may be substituted.

Representatives of this group of substances possessing the highestactivity may be indicated by the formula ##STR9## where R₉ is a hydrogenatom or a methyl group and

R₈ represents a phenyl group which may be substituted with 1-3 halogenatoms, with an alkyl group, with a cyclo-alkyl group, with a nitrogroup, with a tetramethylene group, with a methylenedioxy group or witha methylsulfonyl group.

Examples of compounds having the highest activity are:

N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)urea, melting point at238° C.,

N-(2,6-difluorobenzoyl)-N'-(3,4-dichlorophenyl)urea, melting point 253°C.

N-(2,6-difluorobenzoyl)-N'-(3,4-dichlorophenyl)urea, melting point 197°C.

N-(2,6-dichlorobenzoyl)-N'-(4-chlorophenyl)urea, melting point 236° C.,

N-(2,6-dichlorobenzoyl)-N'-(4-chlorophenyl)urea, melting point190°-191.5° C.

N-(2,6-dichlorobenzoyl)-N'-(2,4-dichlorophenyl)urea, melting point 238°C.,

N-(2,6-dichlorobenzoyl)-N'-(4-cyclopropylphenyl)urea, melting point 208°C.

N-(2,6-dichlorobenzoyl)-N'-(3-chloro-4-iodophenyl)urea, melting point254° C.

N-(2,6-dichlorobenzoyl)-N'-(3-chloro-4-bromophenyl)urea, melting point240° C.

N-(2,6-dichlorobenzoyl)-N'-(4-isopropylphenyl)urea, melting point 204°C.

N-(2,6-dichlorobenzoyl)-N'-(3,4-dibromophenyl)urea, melting point 252°C.

N-(2,6-dichlorobenzoyl)-N'-(4-fluorophenyl)urea, melting point 212° C.

N-(2,6-dichlorobenzoyl)-N'-(3-trifluoromethylphenyl)urea, melting point230° C.

N-(2,6-dichlorobenzoyl)-N'-(4-butylphenyl)urea, melting point 190° C.

N-(2,6-dichlorobenzoyl)-N'-(3-chloro-4-methylsulfonylphenyl)urea,melting point 245° C.

N-(2,6-dichlorobenzoyl)-N'-(4-t.butylphenyl)urea, melting point 212° C.

N-(2,6-dichlorobenzoyl)-N'-(3,4-difluorophenyl)urea, melting point 216°C.

N-(2,6-dichlorobenzoyl)-N'-(2,4-difluorophenyl)urea, melting point 248°C.

N-(2,6-dichlorobenzoyl)-N'-(4-bromophenyl)urea, melting point 236° C.

N-(2,6-dichlorobenzoyl)-N'-(2,5-difluoro-4-bromophenyl)urea, meltingpoint 270° C.

N-(2,6-dichlorobenzoyl)-N'-(4-iodophenyl)urea, melting point 215° C.

N-(2,6-dichlorobenzoyl)-N'-(3-fluoro-4-chlorophenyl)urea, melting point225° C.

N-(2,6-dichlorobenzoyl)-N'-(4-phenylphenyl)urea, melting point 260° C.

N-(2,6-dichlorobenzoyl)-N'-(4-cyanophenyl)urea, melting point 248° C.

N-(2,6-dichlorobenzoyl)-N'-(3-fluoro-4-bromophenyl)urea, melting point228° C.

N-(2,6-dichlorobenzoyl)-N'-(3-fluoro-4-iodophenyl)urea, melting point220° C.

N-(2,6-dichlorobenzoyl)-N'-(2-fluoro-4-iodophenyl)urea, melting point256° C.

N-(2,6-dichlorobenzoyl)-N'-(4-n.propylphenyl)urea, melting point 194° C.

N-(2,6-dichlorobenzoyl)-N'-(4-trifluoromethylphenyl)urea, melting point214° C.

N-(2,6-dichlorobenzoyl)-N'-(3-cyclopropylphenyl)urea, melting point 208°C.

N-(2,6-dichlorobenzoyl)-N'-(2-methyl-4-chlorophenyl)urea, melting point206° C.

N-(2,6-dichlorobenzoyl)-N'-(4-sec.butylphenyl)urea, melting point 168°C.

N-(2,6-dichlorobenzoyl)-N'-(4-iso.butylphenyl)urea, melting point 215°C.

N-(2,6-dichlorobenzoyl)-N'-(4-ethylphenyl)urea, melting point 228° C.

N-(2,6-dichlorobenzoyl)-N'-(4-n.dodecylphenyl)urea, melting point 117°C.

N-(2,6-dichlorobenzoyl)-N'-(4-benzylphenyl)urea, melting point 207° C.

N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)urea, melting point 250°C.

N-(2,6-dichlorobenzoyl)-N'-(methyl)-N'-(3,4-dichlorophenyl)urea, meltingpoint 178° C.

N-(2,6-dichlorobenzoyl)-N'-(ethyl)-N'-(3,4-dichlorophenyl)urea, meltingpoint 154° C.

N-(2,6-dichlorobenzoyl)-N'-(methyl)-N'-(4-t.butylphenyl)urea, meltingpoint 158° C.

N-(2,6-dichlorobenzoyl)-N'-(methyl)-(4-bromophenyl)urea, melting point182° C.

N-(2,6-dichlorobenzoyl)-N'-(ethyl)-N'-(4-bromophenyl)urea, melting point148° C.

N-(2,6-dichlorobenzoyl)-N'-(ethyl)-N'-4-isopropylphenyl)urea, meltingpoint 135° C.

N-(2,6-dichlorobenzoyl)-N'-(ethyl)-N'-(4-n.butylphenyl)urea, meltingpoint 130° C.

N-(2,6-dichlorobenzoyl)-N'-(methyl)-N'-(4-chlorophenyl)urea, meltingpoint 176° C.

N-(2,6-dichlorobenzoyl)-N'-(ethyl)-N'-(4-chlorophenyl)urea, meltingpoint 146° C.

N-(2,6-dichlorobenzoyl)-N'-(ethyl)-N'-(4-t.butylphenyl)urea, meltingpoint 130° C.

N-(2,6-dichlorobenzoyl)-N'-(methyl)-N'-(4-nitrophenyl)urea, meltingpoint 195° C.

N-(2,6-dichlorobenzoyl)-1-(4-chlorophenyl)parabanesaure, melting point157° C.

N-(2,6-dichlorobenzoyl)-N'-(2,4,5-trichlorophenyl)urea, melting point270° C.

N-(2,6-dichlorobenzoyl)-N'-(phenyl)urea, melting point 195° C.

N-(2,6-dichlorobenzoyl)-N'-(4-nitrophenyl)urea, melting point 265° C.

N-(2,6-dichlorobenzoyl)-N'-(4-trifluoromethylphenyl)urea, melting point255° C.

N-(2,6-dichlorobenzoyl)-N'-(4-n.butylphenyl)urea, melting point 193° C.

N-(2,6-dichlorobenzoyl)-N'-(4-t.butylphenyl)urea, melting point 214° C.

N-(2,6-dichlorobenzoyl)-N'-(4-isopropylphenyl)urea, melting point 196°C.

N-(2,6-dichlorobenzoyl)-N'-(3-fluoro-4-iodobenzyl)urea, melting point253° C.

N-(2,6-dichlorobenzoyl)-N'-(3-fluoro-4-chlorophenyl)urea, melting point237° C.

N-(2,6-dichlorobenzoyl)-N'-(3-fluoromethylphenyl)urea, melting point201° C.

N-(2,6-dichlorobenzoyl)-N'-(4-isobutylphenyl)-N'-(methyl)urea, meltingpoint 92° C.

N-(2,6-dichlorobenzoyl)-N'-(4-chlorophenyl)urea, melting point 239° C.

N-(2,6-dichlorobenzoyl)-N'-(4-bromophenyl)urea, melting point 247° C.

N-(2,6-dichlorobenzoyl)-N'-(4-fluorophenyl)urea, melting point 211° C.

N-(2,6-dichlorobenzoyl)-N'-(4-thiomethylphenyl)urea, melting point 202°C.

N-(2,6-dichlorobenzoyl)-N'-(methyl)-N'-(4-chlorphenyl)urea, meltingpoint 124° C.

N-(2,6-dichlorobenzoyl)-N'-(methoxymethyl)-N'-(3,4-dichlorophenyl)urea,melting point 145° C.

To illustrate the high activity of these substances we will mention thatnearly all the above the individually enumerated compounds according tothe invention when used in a concentration of 10 ppm (parts per million)result in a 90-100% kill of larvae of Pieris brassica. Many of the abovesubstances even produce a 90-100% kill in a concentration 3 ppm. Somecompounds, such as

N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(4-chlorophenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(4-butylphenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(4-bromophenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(4-iodophenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(3-fluoro-4-chlorophenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(4-trifluoromethylphenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(3-fluoro-4-bromophenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(2-fluoro-4-iodophenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(ethyl)-N'-(4-bromophenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(4-trifluoromethylphenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(4-n butylphenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(4-t.butylphenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(4-isopropylphenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(3-fluoro-4-iodophenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(3-fluoro-4-chlorophenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(3-trifluoromethylphenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(4-isobutylphenyl)-N'-(methyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(4-chlorophenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(4-bromophenyl)urea,

N-(2,6-dichlorobenzoyl)-N'-(4-fluorophenyl)urea, cause a 90-100% kill ofPieris brassica larvae in a dosage concentration of from 0.1-1 ppm. Thisexceptionally high activity is of prime importance and is to beconsidered as extremely surprising.

A very satisfactory biocidal activity against larvae of the yellow fevermosquito (Aedes aegypti), i.e. a sufficiently killing effect in aconcentration of 0.1 ppm or even less, has been found inter alia inrespect of the following compounds:

N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)urea, melting point 238°C.

N-(2,6-dichlorobenzoyl)-N'-(4-dichlorophenyl)-urea, melting point 236°C.

N-(2,6-dichlorobenzoyl)-N'-(2,4-dichlorophenyl)urea, melting point 238°C.

N-(2,6-dichlorobenzoyl)-N'-(4-cyclopropylphenyl)urea, melting point 208°C.

N-(2,6-dichlorobenzoyl)-N'-(4-methylphenyl)urea, melting point 242° C.

N-(2,6-dichlorobenzoyl)-N'-(fluorophenyl)urea, melting point 212° C.

N-(2,6-dichlorobenzoyl)-N'-(3-trifluoromethylphenyl)urea, melting point230° C.

N-(2,6-dichlorobenzoyl)-N'-(2,5-difluoro-4-bromophenyl)urea, meltingpoint 270° C.

N-(2,6-dichlorobenzoyl)-N'-(3-fluoro-4-chlorophenyl)urea, melting point225° C.

N-(2,6-dichlorobenzoyl)-N'-(4-phenylphenyl)urea, melting point 260° C.

N-(2,6-dichlorobenzoyl)-N'-(4-cyanophenyl)urea, melting point 248° C.

N-(2,6-dichlorobenzoyl)-N'-(4-pentylthiophenyl)urea, melting point 130°C.

N-(2,6-dichlorobenzoyl)-N'-(3-fluoro-4-iodophenyl)urea, melting point220° C.

N-(2,6-dichlorobenzoyl)-N'-(2-fluoro-4-iodophenyl)urea, melting point256° C.

N-(2,6-dichlorobenzoyl)-N'-(4-n.propylphenyl)urea, melting point 194° C.

N-(2,6-dichlorobenzoyl)-N'-(4-sec.butylphenyl)urea, melting point 168°C.

N-(2,6-dichlorobenzoyl)-N'-(4-isobutylphenyl)urea, melting point 215° C.

N-(2,6-dichlorobenzoyl)-N'-(4-ethylphenyl)urea, melting point 228° C.

N-(2,6-dichlorobenzoyl)-N'-(4-n.dodecylphenyl)urea, melting point 117°C.

N-(2,6-dichlorobenzoyl)-N'-(4-benzylphenyl)urea, melting point 207° C.

N-(2,6-dichlorobenzoyl)-N'-(4-trifluoromethylphenyl)urea, melting point214° C.

N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)urea, melting point 209°C.

N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)urea, melting point 217°C.

N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)urea, melting point 250°C.

N-(2,6-dichlorobenzoyl)-N'-(methyl)-N'-(3,4-dichlorophenyl)urea, meltingpoint 178° C.

N-(2,6-dichlorobenzoyl)-N-(methyl)-N'-(3,4-dichlorophenyl)urea, meltingpoint 182° C.

N-(2,6-dichlorobenzoyl)-N'-(ethyl)-N'-(3,4-dichlorophenyl)urea, meltingpoint 153° C.

N-(2,6-dichlorobenzoyl)-N'-(methyl)-N'-(4-bromophenyl)urea, meltingpoint 182° C.

N-(2,6-dichlorobenzoyl)-N'-(ethyl)-N'-(4-bromophenyl)urea, melting point148° C.

N-(2,6-dichlorobenzoyl)-N-(methyl)-N'-(4-chlorophenyl)urea, meltingpoint 124° C.

N-(2,6-dichlorobenzoyl)-N-(methoxymethyl)-N'-(4-chlorophenyl)urea,melting point 122° C.

N-(2,6-dichlorobenzoyl)-N-(methoxymethyl)-N'-(3,4-dichlorophenyl)urea,melting point 145° C.

N-(2,6-dichlorobenzoyl)-1-(4-chlorophenyl)parabanic acid, melting point157° C.

N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)urea, melting point 168°C.

N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)thiourea, melting point169° C.

Examples of other active substances according to the invention are:

N-(2,6-dichlorobenzoyl)-N'-(3-chlorophenyl)urea, melting point 237° C.

N-(2,6-dichlorobenzoyl)-N'-(2,3-dimethylphenyl)urea, melting point 238°C.

N-(2,6-dichlorobenzoyl)-N'-(5,6,7,8-tetrahydro-2-naphthyl)urea, meltingpoint 196° C.

N-(2,6-dichlorobenzoyl)-N'-(3,4-dioxymethylenephenyl)urea, melting point242° C.

N-(2,6-dichlorobenzoyl)-N'-(4-dichlorocyclopropylphenyl)urea, meltingpoint 245° C.

N-(2,6-dichlorobenzoyl)-N'-(4-methylsulphenyl)urea, melting point 222°C.

N-(2,6-dichlorobenzoyl)-N'-(3-bromo-4-chlorophenyl)urea, melting point254° C.

N-(2,6-dichlorobenzoyl)-N'-[4-(p-chlorophenoxy)phenyl]urea, meltingpoint 205° C.

N-(2,6-dichlorobenzoyl)-N'-(3,5-dicyanophenyl)urea, melting point 255°C.

N-(2,6-dichlorobenzoyl)-N'-(3,4,5-trichlorophenyl)urea, melting point270° C.

N-(2,6-dichlorobenzoyl)-N'-(3-chloro-4-methylphenyl)urea, melting point228° C.

N-(2,6-dichlorobenzoyl)-N'-(4-acetylphenyl)urea, melting point 212° C.

N-(2,6-dichlorobenzoyl)-N'-(3-chloro-4-thiomethylphenyl)urea, meltingpoint 242° C.

N-(2,6-dichlorobenzoyl)-N'-(2,5-difluorophenyl)urea, melting point 225°C.

N-(2,6-dichlorobenzoyl)-N'-(4-thiomethylphenyl)urea, melting point 216°C.

N-(2,6-dichlorobenzoyl)-N'-(3-chloro-4-nitrophenyl)urea, melting point300° C.

N-(2,6-dichlorobenzoyl)-N'-(3,4-dimethylphenyl)urea, melting point 202°C.

N-(2,6-dichlorobenzoyl)-N'-(2-fluorophenyl)urea, melting point 205° C.

N-(2,6-dichlorobenzoyl)-N'-(3-fluorophenyl)urea, melting point 222° C.

N-(2,6-dichlorobenzoyl)-N'-(4-dimethylaminosulphonylphenyl)urea, meltingpoint 232° C.

N-(2,6-dichlorobenzoyl)-N'-(3-nitro-4-methylphenyl)urea, melting point256° C.

N-(2,6-dichlorobenzoyl)-N'-(3-methoxyphenyl)urea, melting point 194° C.

N-(2,6-dichlorobenzoyl)-N'-(4-phenylthiophenyl)urea, melting point 196°C.

N-(2,6-dichlorobenzoyl)-N'-(4-benzoylphenyl)urea, melting point 198° C.

N-(2,6-dichlorobenzoyl)-N'-(3-dichlorocyclopropylphenyl)urea, meltingpoint 220° C.

N-(2,6-dichlorobenzoyl)-N'-(4-pentylsulphonylphenyl)urea, melting point167° C.

N-(2,6-dichlorobenzoyl)-N'-(4-n.octylphenyl)urea, melting point 124° C.

N-(2,6-dichlorobenzoyl)-N'-(4-methylthiomethylphenyl)urea, melting point214° C.

N-(2-methoxybenzoyl)N'-3,4-dichlorophenyl)urea, melting point 170° C.

N-(2,6-dichlorobenzoyl)-N'-(methyl)-N'-(phenyl)urea, melting point 138°C.

N-(2,6-dichlorobenzoyl)-N'-(hydroxy)-N'-(2,4,5-trichlorophenyl)urea,melting point 220° C.

N-(2,6-dichlorobenzoyl)-N'-(pentyl)-N'-(3,4-dichlorophenyl)urea, meltingpoint 160° C.

N-(2,6-dichlorobenzoyl)-N'-(acetyl)-N'-(3,4-dichlorophenyl)urea, meltingpoint 180° C.

N-(2,6-dichlorobenzoyl)-N'-(ethoxycarbonyl)-N'-(3,4-dichlorophenyl)urea,melting point 185° C.

N-(2,6-dichlorobenzoyl)-N'-(pentyl)-N'-(4-bromophenyl)urea, meltingpoint 145° C.

N-(2,6-dichlorobenzoyl)-N'-(methyl)-N'-(4-isopropylphenyl)urea, meltingpoint 124° C.

N-(2,6-dichlorobenzoyl)-N'-(pentyl)-N'-(4-chlorophenyl)urea, meltingpoint 138° C.

N-(2,6-dichlorobenzoyl)-N'-(ethyl)-N'-(4-n.propylphenyl)urea, meltingpoint 110° C.

N-(2,6-dichlorobenzoyl)-N'-(ethyl)-N'-(4-sec.butylphenyl)urea, meltingpoint 118° C.

N-(2,6-dichlorobenzoyl)-N'-(ethyl)-N'-(4-isobutylphenyl)urea, meltingpoint 154° C.

N-(2,6-dichlorobenzoyl)-N'-(pentyl)-N'-(4-t.butylphenyl)urea, meltingpoint 82° C.

N-(2,6-dichlorobenzoyl)-N'-(benzyl)-N'-(4-chlorophenyl)urea, meltingpoint 188° C.

N-(2,6-dichlorobenzoyl)-N'-(methyl)-N'-(4-n.butylphenyl)urea, meltingpoint 152° C.

N-(2,6-dichlorobenzoyl)-N'-(n.pentyl)-N'-(4-n.butylphenyl)urea, meltingpoint 104° C.

N-(2,6-dichlorobenzoyl)-N-(methyl)-N'-(methyl)-N'-(3,4-dichlorophenyl)urea,melting point 130° C.

N-(2,6-dichlorobenzoyl)-N'-(methyl)-N'-(4-sec.butylphenyl)urea, meltingpoint 131° C.

N-(2,6-dichlorobenzoyl)-N'-(methyl)-N'-(4-isobutylphenyl)urea, meltingpoint 163° C.

N-(2,6-dichlorobenzoyl)-N'-(methyl)-N'-(4-n.propylphenyl)urea, meltingpoint 146° C.

N-(2,6-dichlorobenzoyl)-1-(p-chlorophenyl)hydantoine urea, melting point183° C.

N-(2,6-dichlorobenzoyl)-N'-(pyridyl-2)urea, melting point 216° C.

N-(2,6-dichlorobenzoyl)-N'-(4-chloropyridyl-2)urea, melting point 197°C.

N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)thiourea, melting point240° C.

By virtue of their activity the substances according to the inventionmay be used to control insects found in agriculture and horticulture,such as caterpillars and beetles, and to preserve textile fabrics, suchas, for example, to protect furs, carpets and textile stocks againstattack by, for example, moths and carpet beetles.

For practical use the compounds according to the invention are worked upinto preparations. In these preparations the active substance is mixedwith a solid carrier material or dissolved or dispersed in a liquidcarrier material, if desired combined with adjuvants, such assurface-active substances and stabilizers.

Examples of preparations according to the invention are aqueoussolutions and dispersions, oil solutions and oil dispersions, pastes,dusts, wettable powders, miscible oils, granules, invert emulsions,aerosol preparations and fumigating candles.

Wettable powders, pastes and miscible oils are preparations inconcentrated form which are diluted with water before or during use.

The invert emulsions are mainly used in air application, large surfacearea being treated with a comparatively small amount of preparation. Ashort time before, or even during, the spraying the invert emulsion maybe prepared in the spraying apparatus by emulsifying water in an oilsolution or an oil dispersion of the active substance. Some forms ofpreparations will now be described in greater detail by way of example.

Granular preparations are produced by, for example, taking up the activesubstance in a solvent, after which granular carrier material, such asporous granules (for example pumice and attaclay), mineral non-porousgranules (sand or ground marl) and organic granules) for example driedcoffee grounds and cut tobacco stems), is impregnated with the solution,as the case may be in the presence of a binder.

A granular preparation may also be produced by compressing the activesubstance together with powdered minerals in the presence of lubricantsand binders and disintegrating and straining the comprimate to thedesired grain size.

Dusts are obtainable by intimately mixing the active substance with aninert solid carrier material in a concentration of, for example, from1-50% by weight. Examples of suitable solid carrier materials are talc,kaolin, pipeclay, diatom earth, dolomite, gypsum, chalk, bentonite,attapulgite and colloidal SiO₂ or mixtures of these and similarsubstances. Alternatively organic carrier materials may be used such as,for example, ground walnut shells.

Wettable powders are produces by mixing from 10-80 parts by weight of asolid inert carrier such as, for example, one of the aforementionedcarrier materials with from 10-80 parts by weight of the activesubstance, from 1-5 parts by weight a dispersing agent such, forexample, as the lignin sulfonates or alkyl naphthalene sulfonates knownfor this purpose, and preferably also with from 0.5-5 parts by weight ofa wetting agent such as one of the fatty alcohol sulfates, alkylarylsulfonates or fatty acid condensation products, for example those knownunder the trade mark Igepon.

To produce miscible oils the active substance is dissolved or finelydivided in a suitable solvent which preferably is poorly miscible withwater after which an emulsifier is added to the solution. Examples ofsuitable solvents are xylene, toluene, high-aromatic petroleumdistillates, for example solvent naphtha, distilled tar oil and mixturesof these liquids. Examples of emulsifiers and alkylphenoxypolyglycolethers, polyoxyethylene sorbitan esters of fatty acids. In thesemiscible oils the concentration of the active compound is not restrictedwithin narrow limits and may vary between, say, 2% and 50% by weight. Inaddition to being a miscible oil the liquid and highly concentratedprimary composition may be a solution of the active substance in asatisfactorily water-miscible liquid, for example acetone, to whichsolution a dispersing agent and possibly a wetting agent has or havebeen added. Dilution with water shortly before or during the sprayingoperation results in an aqueous dispersion of the active substance.

An aerosol preparation according to the invention is obtained in theusual manner by incorporating the active substance, as the case may bein a solvent, in a volatile liquid suitable for use as a propellant, forexample the mixture of chlorine and fluorine derivatives of methane andethane commercially available under the trademark "Freon".

Fumigating candles or fumigating powders, i.e. preparations which whenburning are capable of emitting a pesticidal smoke, are obtained bytaking up the active substance in a combustible mixture which maycontain, for example, a sugar or a wood, preferably in ground form, as afuel, a substance to maintain combustion such, for example, as ammoniumnitrate or potassium chlorate, and furthermore a substance to retard thecombustion, for example kaolin, bentonite and/or colloidal silicic acid.

Besides the above-mentioned ingredients the preparations according tothe invention may contain other substances known for use in preparationsof this type.

For example, a lubricant such as a calcium stearate or magnesiumstearate may be added to a wettable powder or to a mixture to begranulated. Also, "adhesives" such as polyvinylalcoholcellulosederivatives or other colloidal materials, such as casein, may be addedto improve the adherence of the pesticide to the surface to beprotected.

The preparations according to the invention may also include other,known pesticidal compounds. This broadens the spectrum of activity ofthe preparation and may produced synergism.

The following known insecticidal, fungicidal and acaricidal compoundsare suitable for use in such a combined preparation:

Insecticides such as:

1. chlorinated hydrocarbons, for 2,2-bis(p-chlorophenyl)-1, 1,1-trichloroethane and hexachloro-epoxyoctahydrodidmethanonaphthalene;

2. carbamates, for example N-methyl-1-naphthylcarbamate;

3. dinitrophenols, for example 2-methyl-4,6-dinitrophenol and2-(2-butyl)-4,6-dinitrophenyl-3,3-dimethylacrylate;

4. organic phosphor compounds, such asdimethyl-2-methoxy-carbonyl-1-methylvinyl phosphate,O,O-diethyl-O-p.nitrophenylphosphorthionate, N-monomethylamide ofO,O-dimethyl-dithiophosphoryl acetic acid.

Acaricides such as:

5. diphenylsulfides, for example, p-chlorobenzyl and p-chlorophenylsulfide and 2,4,4',5-tetrachlorodiphenylsulfide;

6. diphenylsulfonates, for example p-chlorophenylbenzene sulfonate;

7. methylcarbinols, for example,4,4-dichloro-a-trichloromethylbenzhydrol;

8. quinoxaline compounds, such as methylquinoxaline dithiocarbonate.

Fungicides such as:

9. organic mercury compounds, for example phenyl mercury acetate andmethyl mercury cyanoguanide;

10. organic tin compounds, for example triphenyl tin hydroxide andtriphenyl tin acetate;

11. alkylene bisdithiocarbamates, for example zinc ethylenebisdithiocarbamate and manganese ethylene bisdithiocarbamate;

12. and further:

2,4-dinitro-6-(2-octylphenylcrotonate),

1-[bis(dimethylamino)phosphoryl]-3-phenyl-5-amino-1,2,4-triazole,6-methyl-quinoxaline-2,3-dithliocarbonate,

1,4-dithiocanthraquinone-2,3-dicarbonitrile,

N-trichloromethylthiophthalimide,

N-trichloromethylthiotetrahydrophthalimide

N-(1,1,2,2-tetrachloro-ethylthio)-tetrahydrophthalimide,

N-dichlorofluoromethylthio-N-phenyl-N'-dimethylsulfonyldiamide andtetrachloroisophthalonitrile.

The dosage desirable for practical use of the preparation according tothe invention will naturally depend on various factors, such as thefield of use, the active substance chosen, the form of preparation, thenature and the degree of the infection.

For agricultural use in general a dosage corresponding to from 10-5,000g of active substance per hectare will yield the desired effect.

The compounds according to the invention are new substances which maybeproduced by methods known for the production of similar substances or byanalogous methods. For example, the substances may be produced by

a) reacting a compound of the formula ##STR10## where A, B, X and Y havethe aforementioned meanings, with a compound of the formula ##STR11##where R₁ and R₂ have the aforementioned meanings, so as to obtain acompound of the formula ##STR12## b) reacting a compound of the formula##STR13## where A, B and R have the aforementioned meanings, with acompound of the formula

    R.sub.2 --N═C═O

where R₂ has the aforementioned meanings, so as to obtain a compound ofthe formula ##STR14## c) reacting a compound of the formula ##STR15##where A and B have the aforementioned meanings, with a compound of theformula

    R.sub.2 --NH.sub.2

where R₂ has the aforementioned meaning, and by subsequently hydrolisingthe resulting reaction product, which may be shown by the formula##STR16## so as to obtain a final product of the formula ##STR17## d)reacting a compound of the formula ##STR18## where A and D have theaforementioned meanings, with a compound of the formula

    R.sub.2 --NH.sub.2

where R₂ has the aforementioned meaning, so as to obtain a compound ofthe formula ##STR19## e) reacting a compound of the formula ##STR20##where A and B have the forementioned meanings, with a compound of theformula ##STR21## where R₂ has the aforementioned meanings and arepresents a hydrogen atom or an alkyl group, whilst furthermore thesubstituents a together with the carbon atom bound to them may form acycloalkyl group containing from 3-6 carbon atoms, and subsequentlyacidifying the resulting reaction product, which may be represented bythe formula ##STR22## so as to obtain a compound of the formula##STR23## f) reacting a compound of the formula ##STR24## where A, B andR₂ have the aforementioned meanings, with oxalylchloride, so as toobtain a compound of the formula ##STR25## g) reacting a compound of theformula ##STR26## where A and D have the aforementioned meanings, with acompound of the formula ##STR27## where R₁ and R₂ have theaforementioned meanings, so as to obtain a compound of the formula##STR28## h) reacting a compound of the formula ##STR29## where A, B, R₁and R₂ have the aforementioned meanings, with a compound of the formula

    R.sub.10 --Hal

where R₁₀ is an alkyl group or an alkoxymethyl group and Hal is ahalogen atom, so as to obtain a compound of the formula ##STR30## i)reacting a compound of the formula ##STR31## where A and B have theaforementioned meanings, with a compound of the formula ##STR32## whereR₂ has the aforementioned meaning, so as to obtain a compound of theformula ##STR33## k) reacting a compound of the formula ##STR34## whereA, B and R₂ have the aforementioned meanings, with a compound of theformula

    Cl--CH.sub.2 --O--CH.sub.2 --Cl

so as to obtain a compound of the formula ##STR35##

Amongst these methods the method a is preferably used. The efficiency ofthe method a is satisfactory.

The method a is carried out in the presence of a solvent at a reactiontemperature which may vary from 0° C. to the boiling point of thesolvent used. Examples of suitable solvents are aromatic hydrocarbons,such as benzene, chlorinated hydrocarbons, such as chloroform, methylenechloride or ethylene chloride, or another inert solvent, such asacetonitrile.

The starting product for the method a is obtainable by treating thecorresponding benzamide with oxalylchloride in the presence of a solventsuch as a chlorinated hydrocarbon, for example, methylene chloride.

Examples of other methods of synthesizing the starting products for theprocess a are:

I. reacting a compound of the formula ##STR36## with ammoniumhodanide,so as to obtain a compound of the formula ##STR37## II. heating asolution of a compound of the formula ##STR38## so as to obtain asubstance of the formula ##STR39##

The method b is preferably carried out in a reaction medium containingpyridine and sodium. The reaction is effected at an elevatedtemperature, for example 100° C.

The method c is performed in the presence of a base capable of bindingthe HCl evolved. Examples of suitable bases are triethylamine and3,4-dichloroaniline. The condensation reaction is carried out in thepresence of a solvent, such as benzene, toluene, chlorobenzene,methylene chloride, chloroform or carbontetrachloride. The reactiontemperature may vary between 0° C. and the boiling point of the solventused. The hydrolysis of the intermediate product of the method c maysimply be effected. For example the intermediate product may be exposedto moist air or agitated with water.

The reaction described in the method d takes place in the presence of asolvent. Examples of suitable solvents are xylene, toluene,chlorobenzene and other similar inert solvents having a boiling pointhigher than about 100° C. The reaction is carried out at a temperaturewhich is about equal to the boiling point of the solvent used. Thereaction time is several hours.

In the method c the first step is effected in the presence of a solventsuch as dry benzene. During the reaction, the reaction mixture isslightly cooled. The intermediate product obtained in the first step isacidified by a treatment with, for example, a solution of an inorganicacid in acetic acid. Suitable inorganic acids are HBr, H₂ SO₄, HCl andthe like.

The reaction with oxalylchloride according to the method f is performedin the presence of a solvent. Suitable solvents are aromatichydrocarbons, such as benzene and toluene, and chlorinated hydrocarbons,such as chloroform, carbon tetrachloride and dichloroethane. Thereaction is carried out an elevated temperature, for example at theboiling point of the solvent used.

The reaction according to the method g proceeds in the presence of asolvent, such as a hydrocarbon, for example toluene, and at a reactiontemperature which may vary between room temperature and the boilingpoint of the solvent used.

The process described under the heading h is performed in the presenceof a solvent and a basic substance. A suitable reaction medium is, forexample, dimethylformamide containing an alkalihydroxide.

The reaction according to the method i is performed in the presence of asolvent, such as an either, for example, diethyl ether. The reactiontemperature is preferably about equal to room temperature.

The reaction conditions in performing the method k are the same as thosedescribed for the method h.

The invention will now be described more fully with reference to thefollowing Examples.

1. Production of N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)-urea

9.5 g of 2,6-dichlorobenzamide and 10.34 g of3,4-dichlorophenylisocyanate in 25 ml of pyridine to which 1 g of sodiumhas been added are heated on a steam bath (100° C.+) for 24 hours. Thereaction mixture is poured on ice which contains concentratedhydrochloride acid and the solid precipitate is thoroughly washed withsuccessively water and alcohol. The substance is recristallized fromacetonitrile. Melting point 232° C.

2. Production of N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)-urea

a) Production of 2,6-dichlorobenzoylisocyante

95 of 2,6-dichlorobenzamide are suspended in form 250 to 300 ml of drymethylene chloride. After the addition of 56 mo of oxalyl chloride themixture is slowly heated to boiling point, at which temperature thestarting material rapidly dissolves with a strong evolution ofhydrochloric acid. After boiling for from 15-18 hours the mixture isconcentrated by evaporation in a vacuum. The resulting2,6-dichlorobenzolylisocyanide is used for the next reaction stepwithout further purification.

b) Production of N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorphenyl)-urea

35 g of 2,6-dichlorobenzoylisocyante in 100 ml of dry benzene are addeddrop by drop, with stirring and cooling, to a solution of 24.3 g of3,4-dichloroaniline in 200 ml of dry benzene. Much heat is evolved and aprecipitate is formed which is drawn off while hot and then is washedwith hot benzene. The resultingN-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)-urea is pure, as isshown by thin layer chromatography (with ethylacetate as the solvent).If desired, the product may be recristallized from acetonitrile. Meltingpoint 238° K.

3. Production ofN-(2,6-dichlorothiobenzoyl)-N'-(3,4-dichlorophenyl)-urea

20.6 g of (2-(2,6-dichlorophenyl)-thiazoline-4,5-dione are suspended in250 ml of dry toluene and heated to 90° C. while stirring. Gas isevolved and a violet solution is obtained, to which is added 16.2 g of3,4-dichloroaniline dissolved in 30 ml of toluene. After stirring for 15minutes the solution is cooled and the precipitate obtained is drawnoff. Yield 20.1 g. Melting point 168° C.

4. Production ofN-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)-thiourea

10.5 g of 2,6-dichlorobenzoylchloride are added drop by drop withstirring to a solution of 3.8 g of ammonium rhodanide in 15 ml ofacetone. After boiling for 15 minutes the reaction mixture is added dropby drop to a solution of 8.1 g of 3,4-dichloroaniline in 15 ml ofacetone. After stirring for 30 minutes the reaction mixture is poured inwater and extracted with ether. The ethereal solution is dried andconcentrated by evaporation and the residue is taken up in benzene.After working up and decrystallizing from benzene 1.3 g of thesuperscribed substance is obtained. Melting point 240° C.

5. Production ofN-(2,6-dichlorothiobenzoyl)-N'-(3,4-dichlorophenyl)-thiourea

3.0 g of N-(2,6-dichlorothiobenzoyl)-S-methyldithiocarbamate and 1.6 gof 3,4-dichloroaniline are dissolved in 25 ml of toluene andsubsequently heated while refluxing for 5 hours. The resulting yellowprecipitate is worked up in the usual manner. Yield 2.1 g. Melting point168°-170° C.

6. Production ofN-(2,6-dichlorobenzoyl)-N-(methyl)-N'-(4-chlorophenyl)-urea

10.3 g of N-(2,6-dichlorobenzoyl)-N'-(4-chlorophenyl)-urea and 1.88 g ofpowdered potassium hydroxide (90% are dissolved 40 ml of dimethylformamide, after which 4.7 of methyl iodide are added drop by drop tothe clear solution. The resulting reaction is exothermic. After stirringfor two hours the solution is diluted with ice water and the solidsubstance is isolated. Yield 10.3 g. Melting point 124°-126° C. In acompletely similar manner but using methoxymethylchloride instead ofmethyliodide,N-(2,6-dichlorobenzoyl)-N-(methoxymethyl)-N'-(4-chlorophenyl)-urea isproduced. Melting point 121.5°-122.5° C.

7. Production of3-p-chlorophenyl-5-(2,6-dichlorobenzoyl)-2,3,5,6-tetrahydro-4H-1,3,5-oxadiazinone-4

6.5 g of N-(2,6-dichlorobenzoyl)-N'-(4-chlorophenyl)-urea and 1.3 g of90% powdered potassium hydroxide are dissolved in 25 ml ofdimethylformamide, after which 2.18 of dichlorodimethylether are addedto the solution. After stirring for two hours at 0° C., another portionof 1.3 g of 90% powdered potassium hydroxide is added, after which themixture is stirred for 24 hours at room temperature. After dilution withice water the obtained solid substance is isolated and chromatographed.Yield 2.1 g. Melting point 164°-168° C.

8. Production ofN-(2,6-dichlorobenzoyl)-N'-(4-chlorophenyl)-N'-(cyclohexenyl-1)-urea

3.1 g of 1-(4-chloroaniline)-cyclohexene are dissolved in 50 ml ofabsolute ether and to this solution is added a solution of 3.25 g of2,6-dichlorobenzoylisocyanate in 10 ml of absolute ether. After a shorttime a precipitate is produced which is drawn off and washed with ether.Yield 5.1 g. Melting point 156°-158° C.

9. Production of N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)-urea

A solution of 1.62 g of 3,4-dichloroaniline and 1.01 g of triethylaminein 20 ml of benzene was added drop by drop to a solution of 2.71 g of2,6-dichlorobenzoylisocyaninedichloride in 25 ml of benzene whilestirring at 20° C. There is a slight rise in temperature and a whiteprecipitate is produced. After stirring for two hours the whitesubstance is drawn off and the filtrate is exposed to moist air. After24 hours almost perfect crystals are produced, which are isolated.Melting point 236° C. Yield 1.3 g.

10. Production of N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)-urea

2.62 g of N-(2,6-dichlorobenzoyl)-ethylurethane and 1.62 g of3,4-dichloroaniline are added to 10 ml of xylene and heated at boilingpoint for two hours, the alcohol formed being distilled off. Aftercooling, the crystals formed are filtered off. Yield 3.4 g. Meltingpoint 236° C.

11. Production of 3-(2,6-dichlorobenzoyl)-1-(p-chlorophenyl)-hydantoin

a. Preparation ofN-(2,6-dichlorobenzoyl)-N'-(cyanomethyl)-N'-(p-chlorophenyl)-urea

16.0 g of 2,6-dichlorobenzoylisocyanate are added in small portions to asolution of 11.66 g of p-chloroaniline-acetonitrile in 100 ml of drybenzene with moderate cooling. After some time a substance crystallizesout, which after about 12 hours is drawn off and washed with benzene.After drying the weight is 25.25 g, i.e. 93.7% the melting point being185° C. with spontaneous decomposition on the Kofler heating bench.Thin-layer chromatography (solvent either ethylacetate or chloroform)shows that the substance is pure, however, if desired, it may berecrystallized from 250 ml of benzene with a yield of 80%.

b) Preparation of 3-(2,6-dichlorobenzoyl)-1-(p-chlorophenyl)-hydantoin

25 g of the substance prepared by the method described in 11 a werestirred at room temperature in 150 ml of about 15% HBr solution inacetic acid, the substance dissolving almost completely with the rapidformation of a thick precipitate. After being heated (at 40° C.) for ashort time and being allowed to stand for some hours, the suspension ispoured in half a liter of water, drawn off, washed with water and dried.Yield 24 g. Melting point 176°-180° C.

12. Production of 3-(2,6-dichlorobenzoyl)-1-(p-chlorophenyl)-parabanicacid

10.3 g of N-(2.6-dichlorobenzoyl)-N'-(p-chlorophenyl)-urea are boiled in100 ml of dry 1,2-dichloroethane containing 3 ml of oxalylchloride for24 hours. The urea dissolves with the evolution of hydrochloric acid.After concentration by evaporation and after the addition of 25 ml ofligroin the residue becomes crystalline. The substance may berecrystallized from 30 mls of benzene. Melting point 157° C. Yield 8 g.

It should be noted that the substances enumerated in the specificationwere produced in a manner which is entirely analogous to the methodsillustrated in the above Examples. In producing the large number ofcompounds according to the invention especially the above describedmethod a), which is illustrated by the Examples 2, 3, 4 and 5, isfrequently used.

13. From the substances enumerated in this specification wettablepowders have been prepared by mixing 25 parts by weight of the activesubstance with 3 parts by weight of calciumlignin sulfonate, 2 parts byweight of dibutylnaphthalenesulfonate and 70 parts by weight of kaolin.

14. Liquid concentrates of the active substances according to theinvention have been prepared by dissolving 10 parts by weight of theactive substance in dimethylformamide to which a small amount ofcyclohexanone may be added and by subsequently adding to the obtainedsolution from 6 to 7 parts by weight of an emulsifier, such as a mixtureof nonylphenolpolyglycolether and alkaline-earth alkylbenzenesulfonate.

15. The active substances according to the invention have been dispersedin water in concentrations of 100, 30, 10, 3, 1, 0.3 and 0.1 mg of theactive substance per liter of aqueous dispersion. Young Brussels sproutplants are sprayed with an aqueous dispersion of the substance accordingto the invention to be investigated, until the dispersion drops off.After the plants have dried they are placed in Perspex cylinders andthen each infected with 5 larvae of Picris brassica (caterpillars of theWhile cabbage butterfly). The cylinders are then covered with gauze andstored at a temperature of 24° C. and a relative humidity of from60-70%. After 5 days the mortality percentage is ascertained. Each testis conducted in triplicate. The results of the tests are given in thefollowing Table. The meanings of the symbols used in the Table area:

+=from 90-100% mortality

±=from 50-90% mortality

-=less than 50% mortality.

                  TABLE                                                           ______________________________________                                        Biocidal activity on larvae of Piertis brassica                                            Activity                                                                      concentration expressed in mg of                                              active substance per liter                                       Compound       100    30    10   3   1    0,3 0,1                             ______________________________________                                        N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   +    ±                                                                              -                               N'-(3,4-dichlorophenyl)                                                       urea                                                                          N-(2,6-difluorobenzoyl)-                                                                     +      +     +    +   +    +   -                               N'-(3,4-dichlorophenyl)                                                       urea                                                                          N-(2,6-dimethylbenzoyl)-                                                                     +      ±  ± ±                                                                              ±                                     N'-(3,4-dichlorophenyl)                                                       urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   +    +   +                               N'-(4-chlorophenyl)                                                           urea                                                                          N-(2,6-dimethylbenzoyl)-                                                                     +      +     +                                                 N'-(4-chlorophenyl)                                                           urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    -                                            N'-(2,4-dichlorophenyl)                                                       urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   ± -                                   N'-(4-cyclopropylphenyl)                                                      urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    ±                                                                              -                                        N'-(3-chloro-4-iodo-                                                          phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    -                                            N'-(3-chloro-4-bromo-                                                         phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    ±                                                                              -                                        N'-(4-isopropylphenyl)                                                        urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    -                                            N'-(3,4-dibromophenyl)                                                        urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    ±                                                                              -                                        N'-(4-fluorophenyl)                                                           urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    -                                            N'-(3-trifluoromethyl-                                                        phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   +    -                                   N'-(4-n.butylphenyl)                                                          urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    ±                                                                              -                                        N'-(3-chloro-4-methyl-                                                        sulfonylphenyl) urea                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   +    ±                                                                              -                               N'-(4-t.butlyphenyl)                                                          urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   +    ±                                                                              -                               N'-(3,4-difluorophenyl)                                                       urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   ± -                                   N'-(2,4-difluorophenyl)                                                       urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   +    +   -                               N'-(4-bromophenyl)                                                            urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   -                                        N'-(2,5-difluoro-4-bromo-                                                     phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   +    ±                                                                              -                               N'-(4-iodophenyl)                                                             urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   +    +   -                               N'-(3-fluoro-4-chloro-                                                        phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    -                                            N'-(4-phenylphenyl)                                                           urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   ± -                                   N'-(4-cyanophenyl)                                                            urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   +    +   -                               N'-(3-fluoro-4-bromo-                                                         phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   +                                        N'-(3-fluoro-4-iodo-                                                          phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   +    +   -                               N'-(2-fluoro-4-iodo-                                                          phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    -                                            N'-(4-n.propylphenyl)                                                         urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   +    +   +                               N'-(4-trifluoromethyl-                                                        phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    -                                            N'-(3-cyclopropylphenyl)                                                      urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    -                                            N'-(2-methyl-4-chloro-                                                        phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     +                                                 N'-(4-sec.butlyphenyl)                                                        urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +                                                 N'-(4-isobutylphenyl)                                                         urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +                                                 N'-(4-ethlyphenyl)                                                            urea                                                                          N-(2,6-dichlorobenzoyl)-                                                      N'-(4-n.dodecylphenyl)                                                        urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     +                                                 N'-(4-benzylphenyl)                                                           urea                                                                          N-(2,6-dibromobenzoyl)-                                                                      +      +     ± ±                                                                              -                                        N'-(3,4-dichlorophenyl)                                                       urea                                                                          N-(3,6-dichlorobenzoyl)-                                                                     +      +     +    +   ± -                                   N'-(methyl)-N'-(3,4-di-                                                       chlorophenyl) urea                                                            N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   ± -                                   N'-(ethyl)-N'-(3,4-di-                                                        chlorophenyl) urea                                                            N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   ± -                                   N'-(methly)-N'-(4-t.                                                          butylphenyl) urea                                                             N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   +    -                                   N'-(methyl)-N'-(4-bromo-                                                      phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   +    +   ±                            N'-(ethyl)-N'-(4-bromo-                                                       phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    -                                            N'-(ethyl)-N'-(4-iso-                                                         propylphenyl) urea                                                            N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   -                                        N'-(ethyl)-N'-(4-n.                                                           butlyphenyl) urea                                                             N-(2,6-dichlorobenzoyl)-                                                                     +      +     +    +   ± -                                   N'-(methyl)-N'-(4-chloro-                                                     phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     +                                                 N'-(ethyl)-N'-4-chloro-                                                       phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     +                                                 N'-(ethyl)-N'-(4-t.                                                           butylphenyl) urea                                                             N-(2,6-dichlorobenzoyl)-                                                                     +      +     +                                                 N'-(methyl)-N'-(4-nitro-                                                      phenyl) urea                                                                  3-(2,6-dichlorobenzoyl)-                                                                     +      +     +                                                 1-(4-chlorophenyl)-para-                                                      banic urea                                                                    N-(2,6-dichlorobenzoyl)-                                                                     +      +     ± -                                            N'-(2,4,5-trichloro-                                                          phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     ± -                                            N'-(phenyl) urea                                                              N-(2,6-dichlorobenzoyl)-                                                                     +      +     ± -                                            N'-(4-nitrophenyl)                                                            urea                                                                          N-(2,6-difluorobenzoyl)-                                                                     +      +     +    +   +                                        N'-(4-trifluoromethyl-                                                        phenyl) urea                                                                  N-(2,6-difluorobenzoyl)-                                                                     +      +     +    +   +                                        N'-(4-n.butylphenyl)                                                          urea                                                                          N-(2,6-difluorobenzoyl)-                                                                     +      +     +    +   +                                        N'-(4-t.butylphenyl)                                                          urea                                                                          N-(2,6-difluorobenzoyl)-                                                                     +      +     +    +   +                                        N'-(4-isopropylphenyl)                                                        urea                                                                          N-(2,6-difluorobenzoyl)-                                                                     +      +     +    +   +                                        N'-(3-fluoro-4-iodo-                                                          phenyl) urea                                                                  N-(2,6-difluorobenzoyl)-                                                                     +      +     +    +   +                                        N'-(3-fluoro-4-chloro-                                                        phenyl) urea                                                                  N-(2,6-difluorobenzoyl)-                                                                     +      +     +    +   +                                        N'-(3-trifluoromethyl-                                                        phenyl) urea                                                                  N-(2,6-difluorobenzoyl)-                                                                     +      +     +    +   +                                        N'-(4-isobutylphenyl)-                                                        N'-(methyl) urea                                                              N-(2,6-difluorobenzoyl)-                                                                     +      +     +    +   +                                        N'-(4-chlorophenyl)                                                           urea                                                                          N-(2,6-difluorobenzoyl)-                                                                     +      +     +    +   +                                        N'-(4-bromophenyl)                                                            urea                                                                          N-(2,6-difluorobenzoyl)-                                                                     +      +     +    +   +                                        N'-(4-fluorophenyl)                                                           urea                                                                          N-(2,6-difluorobenzoyl)-                                                                     +      +     +    ±                                                                              -                                        N'-(4-thiomethylphenyl)                                                       urea                                                                          N-(2,6-difluorobenzoyl)-                                                                     +      +     +                                                 N-(methyl)-N'-(4-chloro-                                                      phenyl) urea                                                                  N-(2,6-difluorobenzoyl)-                                                                     +      +     +                                                 N-(methoxymethyl)-N'-                                                         (3,4-dichlorophenyl) urea                                                     N-(2,6-dichlorobenzoyl)-                                                                     +      ±  ± -                                            N'-(3-chlorophenyl)                                                           urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      -                                                       N'-(5,6,7,8-tetrahydro-                                                       2-naphthyl) urea                                                              N-(2,6-dichlorobenzoyl)-                                                                     +      ±  -                                                 N'-(3,4-dioxymethylene-                                                       phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     ± -                                            N'-(4-dichlorocyclo-                                                          propylphenyl) urea                                                            N-(2,6-dichlorobenzoyl)-                                                                     +      ±  -                                                 N'-(4-methylsulfonyl)                                                         urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      -                                                       N'-(3-bromo-4-chloro-                                                         phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      ±  -                                                 N'-4-(p-chlorophenoxy-                                                        phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      ±  -                                                 N'-4-(p-chlorophenoxy-                                                        phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      ±  -                                                 N'-(3,5-dicyanophenyl)                                                        urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      -                                                       N'-(2,5-difluorphenyl)                                                        urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      -                                                       N'-(3,4-dimethylphenyl)                                                       urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     ±   ±  ± -                                            N'-(4-dimethylaminosul-                                                       fonylphenyl) urea                                                             N-(2,6-dichlorobenzoyl)-                                                                     +      +     -                                                 N'-(4-phenylthiophenyl)                                                       urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     ±                                              N'-(4-benzoylphenyl)                                                          urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     +      +     -                                                 N'-(4-pentylthiophenyl)                                                       urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     ±   -                                                       N'-3-dichlorocyclopro-                                                        pylphenyl) urea                                                               N-(2,6-dichlorobenzoyl)-                                                                     +      ±  -                                                 N'-(4-pentylsulfonyl-                                                         phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      ±  -                                                 N'-(4-n.octylphenyl)                                                          urea                                                                          N-(2,6-methoxybenzoyl)-                                                                      +      ±  -                                                 N'-(3,4-dichlorophenyl)                                                       urea                                                                          N-(2-chlorobenzoyl)-                                                                         +      ±  ± -                                            N'-(3,4-dichlorophenyl)                                                       urea                                                                          N-(2-bromobenzoyl)-N'-                                                                       +      +     -                                                 (3,4-dichlorophenyl)                                                          urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                     ±   -                                                       N'-(hydroxy)-N'-(2,4,5,-                                                      trichlorophenyl) urea                                                         N-(2,6-dichlorobenzoyl)-                                                                     +      +     -                                                 N'-(pentyl)-N'-(3,4-di-                                                       chlorophenyl) urea                                                            N-(2,6-dichlorobenzoyl)-                                                                     +      +     -                                                 N'-(acetyl)-N'-(3,4-di-                                                       chlorophenyl) urea                                                            N-(2,6-dichlorobenzoyl)-                                                                     +      +     -                                                 N'-(ethoxycarbonyl)-N'-                                                       (3,4-dichlorophenyl) urea                                                     N-(2,6-dichlorobenzoyl)-                                                                     +      +     ± -                                            N'-(pentyl)-N'-(4-bromo-                                                      phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      ±  -                                                 N'-(methyl)-N'-(4-iso-                                                        propylphenyl) urea                                                            N-(2,6-dichlorobenzoyl)-                                                                     +      +     ± -                                            N'-(pentyl)-N'-(4-chloro-                                                     phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                     +      +     ± -                                            N'-(ethyl)-N'-(4-n.pro-                                                       pylphenyl) urea                                                               N-(2,6-dichlorobenzoyl)-                                                                     +      ±  ±                                              N'-(ethyl)-N'-(4.sec.bu-                                                      tylphenyl) urea                                                               N-(2,6-dichlorobenzoyl)-                                                                     +      +     -                                                 N'-(ethyl)-N'-(4-isobu-                                                       tylphenyl) urea                                                               N-(2,6-dichlorobenzoyl)-                                                                     +      ±  -                                                 N'-(pentyl)-N'-(4-t.bu-                                                       tylphenyl) urea                                                               N-(2,6-dichlorobenzoyl)-                                                                     +      +     ±                                              N'-(benzyl)-N'-(4-chloro-                                                     phenyl urea                                                                   N-(2,6-dichlorobenzoyl)-                                                                     +                                                              N-(methoxymethyl)-N'-(4-                                                      chlorophenyl) urea                                                            N-(2,6-dichlorobenzoyl)-                                                                     +      +     ±                                              N'-(methyl)-N'-(4-n.bu-                                                       tylphenyl) urea                                                               N-(2,6-dichlorobenzoyl)-                                                                     +      +     ±                                              N-(methyl)-N'-(3,4-dichlo-                                                    rophenyl) urea                                                                N-(2,6-dichlorobenzoyl)-                                                                     +      ±  ±                                              N'-(methyl)-N'-(4-sec.                                                        butylphenyl) urea                                                             N-(2,6-dichlorobenzoyl)-                                                                     +      ±  -                                                 N'-(methyl)-N'-(4-isobu-                                                      tylphenyl) urea                                                               N-(2,6-dichlorobenzoyl)-                                                                     +      -                                                       N'-(methyl)-(4-n.propyl-                                                      phenyl) urea                                                                  (3-(2,6-dichlorobenzoyl)-                                                                    +      -                                                       1-(p-chlorophenyl)                                                            hydantoin                                                                     N-(2,6-idchlorobenzoyl)-                                                                     +      +     ± -                                            N'-(4-chloropyridyl-2-)                                                       urea                                                                          ______________________________________                                    

EXAMPLE 16

The substances according to the invention are dispersed in water inconcentrations of 1, 0.3, 0.1, 0.03 and 0.1 mg of active substance perliter of dispersion.

The aqueous dispersion are then inoculated with 20 one day old larvae ofthe yellow fever mosquito (aedes aegypti) and maintained at atemperature of 25° C. The larvae are fed with malt yeast. After 6 daysthe mortality percentage is determined, taking account of the naturalmortality. The results of this test are given in the following Table.The means of the symbols are:

+=from 90-100% mortality

±=from 50-90% mortality

-=less than 50% mortality.

It should be noted that when the mortality percentage is not determinedafter 6 days but after 14 days it is much higher. The mortalitypercentage after 14 days may be derived reasonably satisfactorily fromthe following Table, which relates to a waiting period of 6 days, bychanging the "±" results to "+" results.

                  TABLE                                                           ______________________________________                                        Biocidal activity on larvae of Aedes aegypti                                                Activity                                                                      Concentration expressed in mg of                                              active substance per liter                                      Compound        1       0,3    0,1  0,03 0.01                                 ______________________________________                                        N-(2,6-dichlorobenzoyl)-                                                                      ±    ±   ± ± ±                                 N'-(3,4-dichlorophenyl)                                                       urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      ±    ±   ± ± -                                    N'-(4-chlorophenyl)                                                           urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      ±    ±   ± -                                         N'-(2,4-dichlorophenyl)                                                       urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      +       ±   ± -                                         N'-(4-cyclopropylphenyl)                                                      urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      +       ±   -                                              N'-(3-chloro-4-bromo-                                                         phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      +       +      ± -                                         N'-(4-fluorophenyl)                                                           urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      +       +      +    ± ±                                 N'-(3-trifluoromethyl-                                                        phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      ±    ±   -                                              N'-(4-n.butylphenyl)                                                          urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      +       +      +    +    +                                    N'-(2,5-difluoro-4-bromo-                                                     phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      +       +      +    +    +                                    N'-(3-fluoro-4-chloro-                                                        phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      +       +      +    +    +                                    N'-(4-phenylphenyl)                                                           urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      +       +      +    -                                         N'-(4-cyanophenyl)                                                            urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      +       +      ± ± ±                                 N'-(4-trifluoromethyl-                                                        phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      +       +      +    +    +                                    N'-(3-fluoro-4-iodo-                                                          phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      +       +      +    +    +                                    N'-(2-fluoro-4-iodo-                                                          phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      +       +      +    +    +                                    N'-(4-n.propylphenyl)                                                         urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      +       +      -                                              N'-(3-cyclopropylphenyl)                                                      urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      +       +      -                                              N'-(2-methyl-4-chloro-                                                        phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      +       +      +                                              N'-(4-sec.butlyphenyl)                                                        urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      +       +      ±                                           N'-(4-iso.butlyphenyl)                                                        urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      +       +      ±                                           N'-(4-ethlyphenyl)                                                            urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      +       +      +                                              N'-(4-n.dodecylphenyl)                                                        urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      ±    ±   ±                                           N'-(4-benzylphenyl)                                                           urea                                                                          N-(2,6-dibromobenzoyl)-                                                                       ±    ±   ± ±                                      N'-(3,4-dichlorophenyl)                                                       urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      ±    ±   ± -                                         N'-(methyl)-N'-(3,4-di-                                                       chlorophenyl) urea                                                            N-(2,6-dichlorobenzoyl)-                                                                      ±    ±   ± -                                         N'-(ethyl)-N'-(3,4-di-                                                        chlorophenyl) urea                                                            N-(2,6-dichlorobenzoyl)-                                                                      +       +      +    -                                         N'-(methyl)-N'-(4-bromo-                                                      phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      +       +      +    -                                         N'-(ethyl)-N'-(4-bromo-                                                       phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      ±    ±   -                                              N'-(ethyl)-N'-(4-n.butly-                                                     phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      +       +      -                                              N'-(methyl)-N'-(4-chloro-                                                     phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      +       +      -                                              N'-(ethyl)-N'-(4-chloro-                                                      phenyl) urea                                                                  3-(2,6-dichlorobenzoyl)-                                                                      +       +      +                                              1-(4-chlorophenyl)-para-                                                      banic urea                                                                    N-(2,6-dichlorobenzoyl)-                                                                      ±    ±   ± -                                         N'-(4-methylphenyl)                                                           urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      ±    -                                                     N'-(4-acetylphenyl)                                                           urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      ±    -                                                     N'-(3-chloro-4-thiomethyl-                                                    phenyl) urea                                                                  N-(2,6-chlorobenzoyl)-                                                                        +       ±   -                                              N'-(4-thiomethylphenyl)                                                       urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      ±    -                                                     N'-(3-chloro-4-nitro-                                                         phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      ±    -                                                     N'-(3,4-dimethylphenyl)                                                       urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      +       +      -                                              N'-(2-fluorophenyl)                                                           urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      ±    ±   -                                              N'-(3-fluorophenyl)                                                           urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      +       +      +    -                                         N'-(4-phenylthiophenyl)                                                       urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      ±    ±   -                                              N'-(4-methylthiomethyl-                                                       phenyl)                                                                       N-(2-chlorobenzoyl)-                                                                          ±    ±   ±                                           N'-(3,4-dichlorophenyl)                                                       urea                                                                          N-(2-bromobenzoyl)-                                                                           ±    ±   ± -                                         N-(3,4-dichlorophenyl)                                                        urea                                                                          N-(2,6-dichlorobenzoyl)-                                                                      ±    ±   ± ± ±                                 N'-(methyl)-N'-(3,4-di-                                                       chlorophenyl) urea                                                            N-(2,6-dichlorobenzoyl)-                                                                      +       +      -                                              N'-(pentyl)-N'-(4-bromo-                                                      phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      +       +      -                                              N-(benzyl)-N'-(4-chloro-                                                      phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      +       +      +                                              N-(methyl)-N'-(4-chloro-                                                      phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      +       +      +                                              N-(methoxymethyl)-N'-                                                         4-chlorophenyl) urea                                                          N-(2,6-dichlorobenzoyl)-                                                                      +       +      +                                              N-(methoxymethyl)-N'-                                                         4-chlorophenyl) urea                                                          N-(2,6-dichlorobenzoyl)-                                                                      +       +      +                                              N'-(methoxymethyl)-N'-                                                        (3,4-dichlorophenyl) urea                                                     N-(2,6-dichlorobenzoyl)-                                                                      +       +      -                                              N-(methyl)-N'-(methyl)-                                                       N'-(3,4-dichlorophenyl)-                                                      urea                                                                          N-(2,6-dichlorothioben-                                                                       ±    ±   ± -                                         zoyl)-N'-(3,4-dichloro-                                                       phenyl) urea                                                                  N-(2,6-dichlorobenzoyl)-                                                                      ±    ±                                                  N'-(3,4-dichlorophenyl)                                                       thiourea                                                                      N-(2,6-dichlorothiobenzoyl)-                                                                  +       +      +    ±                                      N'-(3,4-dichlorophenyl)                                                       thiourea                                                                      ______________________________________                                    

What is claimed is:
 1. A compound of the formula ##STR40## wherein: A isa hydrogen atom, a halogen atom,a methyl group, or a methoxy group;B isa hydrogen atom, a halogen atom, a methyl group, or a methoxy group,with the proviso that A and B are not both a hydrogen atom; X and Y eachare an oxygen atom or a sulfur atom; R and R₁ together with the group##STR41## indicated in the above formula form a ring system selectedfrom the group consisting of ##STR42## and R₂ is a substituted orunsubstituted phenyl group or pyridyl group that may be substituted withhalogen, with nitro, with cyano, or with halgoenated alkyl.
 2. Acompound according to claim 1, having the formula ##STR43## wherein Aand B are the same or different and each is a chlorine atom, a fluorineatom or a methyl group; and R₅ represents from 1 to 3 substituents whichare 1 to 3 halogen atoms, a C₁ to C₁₅ alkyl group, a halogenated C₁ toC₁₅ alkyl group, a cycloalkyl group or a halogenated cycloalkyl group.3. A compound according to claim 2, wherein R₅ represents 1 or 2substituents oriented at position 3 or 4 or positions 3 and 4 or thephenyl group.
 4. A compound according to claim 2, wherein said compoundis 3-(2,6-dichlorobenzoyl)-1-(4-chlorophenyl) parabanic acid.
 5. Acompound of the formula ##STR44## wherein: A is a hydrogen atom, ahalogen atom, a methyl group, or a methoxy group;B is a hydrogen atom, ahalogen atom, a methyl group, or a methoxy group, with the proviso thatA and B are not both a hydrogen atom; X and Y each are an oxygen atom ora sulfur atom; R is a hydrogen atom, an alkyl group, hydroxy group, analkoxy group, an alkoxymethyl group, an acyl group, or an alkoxycarbonylgroup; R₁ is a hydrogen atom, an alkyl group, a halogen substitutedalkyl group, an alkoxy substituted alkyl group, an alkylthio substitutedalkyl group, a cyano substituted alkyl group, a 1-cycloalkenyl group, abenzyl group, a halogen substituted benzyl group, a hydroxy group, analkoxy group, an acyl group, an alkoxycarbonyl group, analkoxythiocarbonyl group, an alkylsulfonyl group, or a phenylsufonylgroup; and R₂ is pyridyl group that may be substituted with halogen,with nitro, with cyano, or with halogenated alkyl.